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Lionel Spalding (Glenn Shadix) arrives at the Majestic Hotel, a 5-star Hotel, when he ends up accidentally being hosed by Kyle (Eric Lloyd) and Brian (Graham Sack), much to the stress and disappointment of the hotel manager and the boys' father Robert Grant (Jason Alexander), who gets angry with the boys but they are promised a holiday afterwards, only to be forced to abandon the trip for a third time by the ruthless hotel owner, Mrs. Dubrow (Faye Dunaway), due to the upcoming Crystal Ball where one of the guests is revealed to be a critic from the Le Monde Traveller Organization who they hope will reward the Majestic a sixth star.

Just then, "Lord" Rutledge (Rupert Everett) a jewel thief (who Mrs. Dubrow thinks is the critic), arrives with an orangutan named Dunston, intending to steal the guests' jewelry. Dunston and his deceased brother Samson were trained in thievery their whole lives. Now Dunston has been wanting to escape from Rutledge's poor treatment and life of crime ever since.

Meanwhile, Dunston escapes Rutledge, and is later found by Kyle, who befriends the poor orangutan and promises to keep him safe. Upon finding out about Dunston's presence, Robert calls for an animal control specialist named Buck LaFarge (Paul Reubens) to remove Dunston from the hotel. Rutledge searches the hotel for Dunston, and upon finding him, ties Kyle up. Dunston and Kyle escape to the ballroom where the Crystal Ball is taking place, acquiring a picture of Rutledge, Dunston, and Samson from Rutledge's room. Kyle and Brian show the picture to their dad, and Robert is infuriated when Kyle tells him Rutledge tied him up. Brian and Kyle search for Dunston, avoiding LaFarge and Mrs. Dubrow, while Robert and Rutledge fight in the kitchen. Robert eventually manages to stand up to Mrs. Dubrow, but is fired in the process. However, it turns out that Mr. Spalding, humiliated and injured by Dunston's antics, was actually the critic all along. As a result, he immediately reduces the Majestic to a one-star hotel. Rutledge is arrested and LaFarge apologizes to Dunston, who then slaps him.

In the end, Robert, Kyle and Brian move to Bali, to manage the Majestic hotel there, where they've managed to keep Dunston as a pet. They invite Mr. Spalding over with a complementary room and meals to make up for all the trouble he endured and assure him that nothing will go wrong this time. However, Dunston, in the last scene, causes more trouble by dropping a large coconut on his head.

The film had received overwhelming negative reviews from critics, and holds a 6% rating on Rotten Tomatoes. Despite this, the film received positive reviews from several professional film reviewers, Desson Howe and Rita Kempley of The Washington Post referred to the film by saying "It ain't half bad." and "Plucky, prank-filled family farce" respectively.[1] Kevin Thomas of the Los Angeles Times stated that 'Dunston Checks In' "is a delightful and funny family film of exceptional high style.", "as light as a souffle and just as delicious.", and "plays like a tribute to the resourceful, unpretentious studio productions of the past." giving the film five out of five stars.[2] According to an article published in the Chicago Tribune, "The cast is talented, the hide-and-seek action is silly, and the bond between a sweet little boy and the adorable ape is touching."[3] Faye Dunaway's performance in the film earned her a Razzie Award nomination for Worst Supporting Actress, but did not win the award.